Azodyestuff



vv10 the RN-N \NH-CONHQNNR oon oon n acid having most probably the formula;

"1 with 'azodyestuif components These dy Patented Ne 10,1925.

' U ITE STATES- PATENT oFFlca. j

Brennan s'rtissnn,; or xoLn-nnurz. ABBIGIN'OB 'ro amen-unmitvoma. rrunnn. Barns AND 00., or-Lnvnaxusnn, um coLoenn-en-rnn-nmnn.

GERMANY.

' 1a Drawing.

citizen of Germany, residing at Koln-Deutz,

in the State of Prussia, Germany, have mvented new I and useful Improvements in Azod' estuifs, ofwhich the following is a speci cation.

My invention relates to new and valuable azodfyestuifs for cottonhaving most probably ormula: I

recess for their production consists in com inin the tetrazo'compound of the.

' 4.4-diamino iphenylurea- 3.3 dicarboxylic .stufl's can also be obtained by 'comb'imn either theB-nitrQQ-aminobenmic, acid wit an azodyestufi component; reducing; the I mg tetrazo solution 204 arts {.of. 1 phenyl- 5; pyraz'olon 3 carboxy nitrogroup 5 in" :this azode tothe amino 3! grou and =final1y,produc1ng' with the aid of p osgene the correspopdmg 8 the. usual manner or by eomb mg 51161 amind-Q-aminobefizoi acid with an azol dyestufi' component, splitting of the acidyl group meta 45 powders solub e in water and in'coneentrated sulfuric acid generall with from a yellow .to' violet coloration.

and, afterwards treating 'azo- My new dyestu s-arexafter beingi-dried ulverized in the 'sha and salts of their alkali enerally ye owish to black e yield upon 'reduction with stannous 'chlori e and hydrochloric acid, 4.4! diaminodiphe'nylurea 3.3 dicar-- 5 boxylic acid] and aromatic amines.

' aminophenyl 3- meth' l- 5 pyrazolon disdyes cotton directly yellow med ghichhwhen aftertreatedsh'wz'itblg g f tee an intooran' a j ast to. light and tz washing. a P J Application flledhprll 15,1924. semi Io. roe-gas.

' In order to illustrate my invention more fully, the followin example is given, the parts being by weig t:- I I Ewa le Ir-"330 parts 4.4'-diam'.inodipheny urea-3.3'-dicarboxylic acid are tetra'zotized in the usual manner with 138 arts 'of sodium nitrite and 500 parts of ydrochloric acid. 19 B. To the resultmg tetrazo solution 378 parts of l-metasolved in water-and ydrochloric acid are added and then this solution is rendered- -alkaline with sodium carbonate. After the' formation of the dyestufi is complete it is salted out, filtered ofi' anddried. The d e 5' is after being dried and ulverized in t e shape of its sodium salt a rownish powder soluble :in water with 'a yellow coloration andin concentrated sulfuric acid with a yellow coloration. It ields upon reduction with stannous chlori eand hydrochloric acid 4.4. 'diaminodiphenylurea 3.3 div carboxylc acid and H l-meta-amino henyl-- 3 methyl 4 amino ,5 l dn'. It

shades Example 2-5-33) arts of 4;4'-d-ia-.m'i j phenyl urea-3.3 ioarboxylic acid re tetrazotized a he usual manner with '138 arts of nitrite and 500 parts ofydrochloric acid 19 B. To the resultin a solution of'sodium'acetateareadded and i then sodium acetate is added to neutralize the mineral acid and leave the; solution vweal. 'y,;aci'tl withuwetie acid and after the formation of the intermediate-Pm uct' is; complete-it is'rendered alkalin'e'wlth carbonate. .207

m phenyl-urea-8.3-dicarboxylic acid are tetraz- I otized in the usual manner with 138 parts plete the dye is salted out, filtered off and dried. The dye is after being dried and a bI'OWlllSh powder.

pulverized in the shape of its sodium salt d-dH-N- N NH-OO-NH N-m-rin boon do coon OOH I 5 It dyes cotton directly yellowish-red shades and to washing.

Ewample 3.-330 parts of h -diaminodiof sodium nitrite and 500 parts of hydrochloric acid 19 A B. To the resulting 'tetrazo solution 221 parts of aceto-aceticanilide-para-carboxylic acid dissolved in water and sodium carbonate are added and then sodium acetate is added to neutralize the mineral acid and leave the solution weakly acid with acetic acid. The acetow It dyes cotton directly yellow shades which when aftertreated with copper sulfate change into greenish-yellow shades very fast to light and to washing.

I claim:

1. The herein described new azodyestutfs, which are after being dried and pulverized in the shape of'their alkali metal salts yellowish to black powders soluble in water and in concentrated sulfuric acid generally with from yellow to violet coloration, yielding .acetic-anilide-pararcarboxylic acid has the formula:

CHs-C o-oH,-co-NH- 000];

After half an hours stirring the solution is rendered alkaline with sodium carbonate. Subsequently 207 parts of aceto-acetic-orthoanisidide in glacial acetic acid are added and the mixture is rendered alkaline. After the formation of the d estufi is complete it is filtered OE and drie The dye is after being dried and pulverized in the shape of. its sodium salt a yellowish-brown powder.

upon reduction with stannous chloride and OOH which is after being dried and pulverized in the shape of its sodium salt a brownish powder soluble in water with a yellow ton yellowish-red shades which by an aftercoloration and in concentrated sulfuric acid treatment with copper sulfate change into with a yellow 'co1orati0n,-yie1ding upon re-' orange shades very fast to light and to 10 duction with stannous chloride and hydro washing, Substantially as described.- chloric acid 4.4-diaminodipheny1-urea-3.3'- In testimony whereof I have hereunto set dicarboxylic acid and l-meta-aminophenylmy h -n I 3-methyl-4-amino-5-pyrazol0n; dyeing cot- 1 RICHARD STUS SER 

